Big Brothers and Big Sisters
by imhookedonaswan
Summary: Killian and Emma are Big Brother and Big Sister to Bellamy and Clarke, little do they know Bell and Clarke are trying to get them together
1. Art Classes and Radio Stations

Emma sighed and checked her watch waiting in the park she and her Little Sister had agreed to meet in and sighed. Her Little was running late and Emma questioned whether this was the best idea, she wasn't exactly a people person and the idea of hanging out with a seventeen year old and being a mentor was becoming more and more intimidating. But Clarke seemed like a good kid, caring and determined and smart as hell according to her file that Emma got about her. Emma looked up and saw a blonde teenaged girl walking towards her and stood up off the bench she was sitting on.

"Are you Clarke Griffin?" she asked the girl who was looking at her skeptically.

"Yeah are you Emma Swan?" the girl asked.

"Yeah, um I guess I'm your Big Sister," Emma said awkwardly holding out her hand for Clarke to shake. Thankfully Clarke took it and shook her hand smiling softly.

"So what did you have in mind? To bond I guess," Clarke asked putting her hands in the pockets of her jacket.

"I saw there were painting lessons at a nearby art supply store that might be fun, since it said in your file you like to draw and stuff, would you want to do that?" Emma asked hoping Clarke would say yes because she had no idea of what else to do that didn't sound completely unoriginal.

"Yeah that'd be fun, let's do it," Clarke said and the both of them started walking the few blocks to the store and making small talk about food and TV shows and Emma starts growing more comfortable and it seems like Clarke does too as they enter the art store happily talking about the upcoming Agent Carter miniseries.

"She was seriously one of the best parts of the first Captain America movie," said Clarke sitting down at one of the easels that were set up around a bowl of fruit that they were supposed to be painting. Emma agreed and sat down next to her and picked up a paintbrush and paused trying to remember everything her favorite high school art teacher taught her before she had to transfer to another school and another foster family. She looked over at Clarke's and saw that the girl was busily painting base coats for the fruits and the bowl, Emma could already tell hers was going to be amazing. They painted together side by side, not saying much to each other both too focused on their paintings, every so often the instructor would walk around and look at people's paintings and offer suggestions. After Emma put the finishing touches on her painting she looked over at Clarke's to see a beautiful painting done in black and white with varying shades of grey.

"That's amazing kid, I didn't know you were that talented," Emma said as she stood up off her stool and placed her canvas over in the corner of the room to dry.

"Thanks, yours is pretty good too," Clarke said placing her canvas next to Emma's, "I can show you some different techniques if you want, for next time."

"Yeah that'd be great, I haven't painted much since high school, it feels good to do it again. Now what do you say to getting a coffee and a snack or something while these dry?" Emma asked.

"Sounds great, I was getting a little hungry," Clarke said as they walked out of the store to a nearby Starbucks.

"So what are your favorite subjects in school?" Emma asked as they sat down at a small table by the window.

Clarke took a sip of her latte and thought for a moment, "The classes at my high school are all okay but I really like the Political Science class I'm taking at Bunker Hill," she said.

"You're taking college classes while still in high school?" Emma asked breaking off a piece of the banana bread they were sharing.

"Yeah it's actually not that bad, one of my friends, Monty, is also taking an engineering class there so it helps to have someone I know there," Clarke said. "What did you do again?"

"I'm a bail bondsperson," Emma said taking a drink from her mocha.

"That sounds intense," Clarke observed.

"It can be, but it pays the bills," Emma shrugged and checked her watch, "I think our paintings should be dry by now, want to go pick them up and then I can take you home?" Emma asked finishing off her drink.

"Sure," Clarke said standing up and taking the last bite of banana bread and smiling. They walked back to the art store and grabbed their paintings and loaded them into Emma's bug and Clarke gave Emma her address as they settled into their seats, Emma switching on the radio to her favorite radio station that was currently playing "Blank Space" by Taylor Swift.

"Oh turn it up I love this song!" Clarke said buckling her seatbelt and smiling. Emma chuckled and turned it up and began driving. Soon they were both singing along at the top of their lungs and laughing.

"GOTTA LONG LIST OF EX-LOVERS THAT'LL TELL YOU I'M INSANE, BUT I'VE GOT A BLANK SPACE BABY AND I'LL WRITE YOUR NAME!" they both sang with large smiles on their faces.

"All right mates that was "Blank Space" by Taylor Swift, now I never really liked this girl's music but I have to admit, this song and the whole album is brilliant. Seriously give it a try, she might surprise you. I'm Killian Jones for WUMD radio and up next is we have some Arctic Monkeys hope you all enjoy," the voice from the radio says.

"Taylor Swift to Arctic Monkeys? This guy is kind of all over the place isn't he?" Clarke says turning down the music a bit.

"Yeah but that's kind of what I like about it, he just plays whatever he wants," Emma said pulling in front of Clarke's house. They get out and pull their paintings out of the back seat, Clarke holds out her painting to Emma.

"Here I want you to have this, so that you can remember our first outing together," she said pushing the canvas into Emma's hands. Emma looked at her and smiles softly, holding out her own painting to Clarke.

"Then I guess you should have mine, a gift from your Big Sister." Clarke smiled and took the canvas.

"Thanks Emma and thanks for taking me out," she said

"Do you want to do something next weekend? Go down to the harbor maybe?" Emma asked.

"Yeah I'd like that," Clarke said, turning and walking to her front door. She turned and waved before unlocking her door. Emma smiled and waved back to her before getting back into her car.

Bellamy rushed into the radio station, dropping his backpack on the floor and flopping onto the couch in the waiting room.

"Hey Bell, how was school?" David asked from his big comfy armchair as he waited for Killian to finish his show.

"Eh same shit different day, is my Big Brother ready to bond and mentor me?" Bellamy asked.

"Yeah he's wrapping up his show now," David replied looking over as Killian unlocked the heavy door to the studio and walked into the waiting room.

"Hello Lad, you ready for me to instill my knowledge of the world onto you?" Killian said a wide smile spreading over his face. Bellamy picked up his backpack and followed Killian into the back room. After having Killian as his Big Brother for 3 years, they had settled into a routine: Bellamy does some homework while Killian listens to new music to play during his show. Killian has even been asking for his input about new music, Bellamy was shocked when Killian had asked his opinion of a new band, he was very much a person who liked to make his own decisions about what to play during his show.

"So I heard you actually played that Taylor Swift song," Bellamy said smirking at Killian.

"What can I say? It's a pretty good song, tell Octavia thank you and happy birthday from me," Killian said with a sly smile.

"I will, if I ever get through this Political Science homework," Bellamy pouts and pulls out his laptop and Poli Sci text book.

"Bloody Hell what are they teaching you kids these days?" Killian says picking up the text book and weighing it in his hands.

"How to run the world apparently, and this one girl in my class probably will someday," Bell says opening his laptop to look at the essay prompt.

"Oh so there's a girl?" Killian teases and Bellamy glares at him.

"It's nothing, just some blonde girl who is so freaking smart and diplomatic she may end up being the next damn president."

"Well remind me to vote for her," Killian jokes and grabs so CDs he still needs to review from a shelf and heads to his desk and plops down in his chair.

"You'd need to be an America citizen to do that you know."

"Ah well just vote for her twice I suppose, now get to doing that homework College Boy," Killian says putting a CD in the player and filling the space with whatever new up and coming band's CD it was. Bell set to work writing his paper, getting it half finished before Octavia texted asking to be picked up from the mall.

"Hey Killian you mind giving me and O a ride home?" Bellamy asked.

"Not at all mate, you want to grab some food on the way home?"

"Sure, let's get some Chinese," Bellamy said saving his essay and putting his laptop and textbook in his backpack and slinging it over his shoulder. Killian drove them to the mall to pick up Octavia and they stopped at their favorite take out place to get their food before Killian dropped them off in front of their apartment building.

"Thanks Killian," Octavia called behind her as she let herself into the building.

"Your welcome lass," Killian said waving to her, "Hey Bell, did you want to go sailing next weekend? After the show?"

"Yeah that sounds great, I'll see you then," Bellamy said walking behind his sister and into his apartment.

**AN:**** So I hope you guys like this, it's been percolating in my head for a while but because of finals and traveling home I haven't gotten a chance to sit down and write it out. **


	2. A Day on the Harbor

**A/N: I am so sorry this took so long to update, between finals and the holidays I barely got a chance to sit down and write and when I ****_was_**** able to write I had a massive case of writers block. Anyway I hope you all enjoy!**

"Bellamy swab that deck, we'll be having customers soon," Killian called out and saw Bellamy straightening cushions on the seats on the front of Killian's sailboat.

"How many people do we have today?" Bellamy asked.

"Just two for a short little lunch tour, they should be here any minute actually," Killian said checking his watch.

"You know I'm pretty sure it's against Big Brother protocol to make your Little Brother work weekends with you," Bellamy said jokingly.

"Oh you love it you git, now come on we have to get this old girl into ship shape before our guests arrive," Killian said clapping Bellamy on the back before heading down into the galley to get the two picnic baskets that he packed for the customers and for he and Bellamy. He swallowed a little nervously, he preferred when larger groups of people took boat tours since it allowed him and Bellamy to stay off to the side or at the helm and let the customers talk amongst themselves, however with only two patrons he and Bellamy would have to really interact with these people and show them a good time but he knew that he and Bell could be charming and charismatic when they needed to be and that they could show these customers a good time.

"Killian you coming?" he heard Bellamy's gruff voice ask from above deck. He grabbed the picnic baskets and hurried up the steps onto the deck of his boat. He set the baskets down onto the little table Bellamy had set up and turned around.

"Are you ready to be a charming lad to our guests?" he asked.

"Yes I'll be the picture of charm, don't you worry," Bellamy said somewhat sarcastically but Killian let it slide, spotting two blonde figures coming towards the boat.

"I think this is them, grab the clipboard to make sure mate," Killian asked, Bellamy handed him his clipboard that had the client's information on it and looked at the names "Emma Swan and Clarke Griffin" interesting names.

"Hi is this the Jolly Roger?" one of the blonde women asked looking up at him.

"Yes it is lass, are you Emma Swan?" he asked his face cracking into a large smile.

"I am, and this is my Little Sister Clarke," she said gesturing to Clarke who smiled and waved at Killian.

"Well let's get started since we have the wind in our favor, right this way," Killian said as he helped them up the small stairs and onto his boat. "Behold the Jolly Roger!"

Emma smiled and looked around the sail boat and at Clarke to gage her reaction to it. The younger blonde looked around the boat and smiled back at Emma; Emma let out a small breath of relief glad that Clarke seemed to be enjoying herself. Killian took his place behind the helm and started the motor and pulled them out into the harbor.

"Bellamy come out of your hiding place and hoist the mainsail and tighten down the jib," Killian called out. Bellamy lumbered out of the cabin and locked eyes with Clarke and froze for a second.

"Hey Princess," he said sarcastically, Clarke rolled her eyes and went to find Emma at the front of the sailboat. Killian cocked an eyebrow at Bellamy, a clear questioning look on his face.

"That's the girl I was telling you about, from my Poli Sci class the one who will rule the world," Bellamy explained.

"Ah and I see that all is not well in paradise," Killian teased.

"She's just so damn stubborn, nobody can say anything she doesn't agree with, hell even the professor isn't safe from her," Bellamy said.

"Be that as it may, she and that Swan woman are customers so be decent."

"Fine, but only for you Big Brother," Bellamy said sarcastically.

"I'll let the sarcasm slide, just go tell them lunch is ready if they want it," Killian ordered as he guided his boat into calm water.

"So how are you liking this so far?" Emma asked as Clarke walked up to her at the front of the ship.

"I have to admit when you said lunch on the harbor I didn't think you meant actually eating on the harbor," Clarke smiled.

"I thought I'd surprise you plus I've kind of always wanted to do this and I found a great deal," said Emma. Clarke smiled and thought to herself how nice it was to have someone who had time to do nice bonding type things with her

"Lunch is ready, if you want to make your way over to the helm to eat," said the boy in her Poli Sci class said and lead them back to where the boat's wheel was and were the captain was lounging on one of the benches.

"Do you know him?" Emma asked Clarke looking after the boy.

"Yeah that's Bellamy he's in my Poli Sci class," Clarke said with a slight edge to her voice.

"I'm guessing there's some tension there."

"I guess you could say we have differing viewpoints on some key issues," Clarke said carefully, deciding to leave out the fact that most classes end up being a debate between the two of them while the rest of the class watches, before stepping down into the little area behind the ship's wheel and pulling a picnic basket towards her and Emma. Bellamy sat down next to her, smirking at her. They all started eating and making polite conversation, the captain putting on some music.

"Interesting mix," observed Clarke.

"I like a little variety in my music, you can't just listen to the same kind of music all the time. I like to switch it up when I DJ," he answered her.

"You DJ?" asked Emma popping some grapes in her mouth.

"Yeah I'm on WUMD," he said stealing some of her grapes.

"Wait you're not _that _Killian Jones, are you? From the Pirating Hour?" Emma asked incredulously.

"Ah so you've heard of me?"

"Yeah but what is with the pirate motif? The Pirating Hour, The Jolly Roger?" Emma asked smirking at him, Clarke watched as they continued to banter.

"Ten bucks says he gives her his number," a low and gravelly voice said in her ear.

"I see your ten bucks and raise you 2 debate free lectures that she doesn't take it. I may not know her that well but good lord does this woman have walls," said Clarke turning to Bellamy.

"Wait how do you not know her? I though she's your sister," Bellamy inquired.

"From the Big Sister/Little Sister program," she answered.

"No way, I'm part of that program too Killian's my Big Brother," he said excitedly.

"Small world, now shush let's watch your Big Brother try to hit on my Big Sister," she said turning back to Killian and Emma.

"I'm telling you Swan, the real Captain Hook is much much cooler than the Disney version," Killian said somewhat desperately.

"You can keep saying that but to me Captain Hook will always be the guy with a perm and a waxed mustache," Emma answered cooly.

"And I take it those are bad things?" he said with a cheeky smirk and a raised eyebrow.

"Oh my god he has no game," Bellamy said softly and massaged his brow with his hands.

"Like you do?" Clarke said rolling her eyes at him.

"Hey I at least know to keep the nonsensical idolization of Captain Hook to myself until at least the 3rd date," he replied with a smirk to match Killian's. Clarke looked over to her Emma and Killian watching him try to flirt with her and her try to keep her walls up.

"What do you say we make this bet a little bit more interesting?" she said to Bellamy.

"I'm listening."

"If your game is as good as you say it is, then it should be no problem to get Killian and Emma to go on one date," she challenged him.

"True, but what do I get if I win?"

Clarke thought for a moment, "The satisfaction of knowing you set your beloved Big Brother up with an awesome date?"

"Try again, Princess," he laughed.

"Ok fine, you know that big paper we have due before finals? The one where we have to debate a topic that we don't agree with? I can help you write it, _help_ being the operative word here," she said after a moment of thought.

Bellamy thought for a moment then said "Deal," and held out his hand for her to shake. She shook it firmly. "We can settle the terms and conditions after class on Monday," she said and he nodded.

"Oi Bell, come on we have to get these ladies back to shore," Killian said coming up to him and clapping him on the back.

"That'll be my cue but until Monday Princess," Bellamy said to Clarke. He climbed up to the top of the cabin to adjust some sails so they could catch more wind quickly taking them back to the docks.

"Well ladies that concludes this harbor cruise, hope you enjoyed it," said Killian as they stepped off the boat and onto the dock, "Oh and Swan," he called causing Emma to turn around Clarke tried to act like she wasn't eavesdropping "In case you want another cruise or a direct line to recommend music on the radio," he said placing a scrap of paper in her palm. Clarke saw Emma freeze and found herself silently hoping she would take it.

"Thanks but I don't think I need it," she said and pushed the scrap back towards Killian, Clarke groaned inwardly when she saw Killian's crestfallen face. Bellamy really had his work cut out for him.


	3. A Little Digging

Big Bros/Big Sis Ch. 3

Emma drove her and Clarke home silently mulling over what had just happened. Had Killian Jones, radio personality and (apparent) harbor cruise captain really just given her his number? And had she really not taken it? She mentally kicked herself for not taking it but she panicked when he gave it to her, she hadn't felt so connected to anyone like that since Neal and no she was not going to think about him right now, she was done thinking about his stupid traitor ass, she thought as she gripped her steering wheel tighter.

"Are you okay?" Clarke asked her pointing to her hands which were white knuckling the wheel. Emma let our a breath and loosened her grip.

"Yeah just peachy," Emma answered keeping her eyes on the road.

"You don't sound like it, why didn't you take Killian's number? You guys seemed to really hit it off," Clarke questioned.

"I just didn't," Emma shrugged hoping Clarke would drop it.

"But why? It just doesn't make sense, you two were practically making eyes at each other."

"Look I didn't take his number because I don't date" Emma said her patience thinning.

"Okay but why? I mean you could I you wanted to," pressed Clarke.

"Because I just don't all right! I have my reasons that I really don't want to discuss with some sixteen year old I've only known for 2 weeks so can you just drop it?" Emma snapped instantly regretting it when she saw the look on Clarke's face.

"Okay fine we won't talk about it," Clarke said putting her hands up in defeat. They drove in silence for a while before Emma sighed.

"Kid I'm sorry, I shouldn't have snapped at you like that," Emma said sneaking a quick glance at Clarke.

"I'm sorry too, I shouldn't have been so pushy," Clarke said "So are you excited for Agent Carter to come out on Tuesday?"

"Yeah I'm making sure to record it since I'm closing in on a perp and I might not be able to watch it live," Emma said turning down Clarke's street.

"Don't worry I won't spoil it for you, I'll see you soon," Clarke said unbuckling her seatbelt.

"See you," Emma said watching Clarke walking up to her front door with a slight pit in her stomach. She really shouldn't have snapped at her like she did, but she supposed it had to look weird that she may or may not have spent the afternoon flirting with someone only to reject them once they got back to dry land. She reached for the swan charm she wore around her neck, squeezing it softly trying not to remember the last time she let her guard down around someone. She mentally shook herself putting her bug into gear and heading home to the bottle of wine and the stack of files on her desk that had her name on them.

Bellamy clenched his fist listening to Clarke prattle on about some current event or another. He glanced at the clock relieved that there was only 5 minutes left of class, he could see that Professor Kane wrapping up class. Bellamy saved his notes and closed his laptop, shoving it in his backpack, when he looked up he saw Clarke standing before him.

"You ready?" she asked, Bellamy could feel his friend Murphy staring at him but he can worry about him later.

"Yeah so do you want to go to the library or something?" Bellamy asked getting up from his desk. She nodded and they walked across campus together and found a quite corner of the library to work in.

"So tell me about your big brother, what he likes, what he doesn't like, any past girlfriends, stuff like that," Clarke says as she pulls out a notebook and pen.

"What are you actually going to take notes?"

"Yeah believe me you're going to need all the help you can get," Clarke said pointedly clicking her pen and placing it to her notebook.

"Well all right then. Um he likes music, sailing, rum, something he likes to call 'good form' and he doesn't like cowards, huge messes, crocodiles, and mushrooms."

"Mushrooms?"

"Yeah he can't stand them for some reason. As far as exes I know there was one woman, Milah or something, that really broke his heart."

"What happened?"

"She was apparently married to someone else and when Killian found out he was just devastated, he really loved her but couldn't stand the fact that she was just using him for flings and fun," said bitterly. "He just kind of went off the deep end after her husband found out and moved them across the country. Drank too much and slept around a bunch, there were a couple of times I had to go over to his place and pry him out of bed so he would go to his shift at the radio station."

"Wow that sounds really awful, but he seems like he's in a better headspace," Clarke said looking up at Bellamy from her notebook.

"Yeah I think just going to the station, doing the harbor cruises, and getting a couple of house plants helped take his mind of things, oh yeah that's another thing he likes, his fucking house plants."

"I'm guessing you're not a big fan of the house plants are you?" Clarke said with a small laugh.

"I didn't mind them when it was one or two succulents but now they are literally all over his place," Bellamy said a little smile spreading over his face.

"Also why does he do the harbor cruises? Like I get that he likes to sail but why take tourists out around the harbor?"

"It's a pet business, he and his older brother started doing them when they first moved out here for some of the bigger companies, so tell me about Emma," he said, "What was up with her not taking Killian's number?"

"I don't know, I asked her about it and she snapped at me. I told you she has some pretty high walls, but I did find out some things while hanging out with her. She likes to paint or she did at one point but she hasn't been able to for awhile, she's a bail bonds person, and she loves Taylor Swift, Law and Order: SVU, she's really excited for Agent Carter, and apparently she likes the water," Clarke said.

"That's all you know about her? I mean I know my work is cut out for me but come on!"

"Hold on, there's also this great thing called Google and Facebook and I did a little digging," she said and reached into her bag and pulled out her own laptop pulling up some articles she had bookmarked and Emma's Facebook profile. "So according to this article she was abandoned on the side of a highway when she was a baby,"

"Shit," said Bellamy furrowing his eyebrows at the computer screen.

"Yeah it doesn't get much better, it looks like she was in foster care and moved around a lot. See her name keeps cropping up in different articles from schools all over the place, but after a certain point she just falls off the radar. Now from her Facebook page I was able to get more on her likes and dislikes and what she likes to do for fun, she really loves action movies and surprisingly Disney movies and also goes to a kickboxing/MMA gym. Her favorite comfort food is grilled cheese and her favorite restaurant is that Granny's dinner down on 3rd street, according to a glowing yelp review she posted."

"You know if you weren't helping me out I'd be a little scared of your stalking skills," said Bellamy leaning back in his chair.

"I'll take that as a thank you," replied Clarke as she closed her laptop and started putting it in her bag.

"Wait where are you going? Aren't you going to help me figure out a way for them to meet again?"

"No, that's for you to figure out Mr. 'I have more game than my Big Brother.' Have fun," she said with a wicked smile before walking out of the library leaving Bellamy stunned in his seat for a few minutes before Octavia called him asking where he was. He gathered up his stuff still thinking of that wicked smile.


	4. Kickboxing and Bar Nights

Emma punched her heavy bag fiercely following with a roundhouse kick to its side.

"Keep your elbows in and control your kicks," her instructor said to her and Emma nodded before facing her bag and repeating the combination. She couldn't help her frustrations, she couldn't get Killian's hurt face or Clarke's words out of her mind and felt another pang of guilt for speaking so harshly to her. It wasn't Clarke's fault that she had a supreme douchebag ex-boyfriend who left her holding stolen property and set her up to take the fall for his crime. It wasn't Clarke's fault she had to go to jail for a crime she didn't commit alone and confused. Her next roundhouse kick sent her bag swinging to the side and the rest of the class turned to look at her.

"Sorry," she said dragging her bag back into place and tried to just keep her mind on her form and off her past relationships. When class ended she took her time taking off her gloves and hand wraps, listening to the few other people in her class chatter about what ever they were doing over the weekend but keeping to herself. A bag dropped to the floor in front of her and Emma looked up at her instructor Mulan.

"Ok you've been taking this class for years and you only lose control like that when something is really on your mind," Mulan said her voice tinged with concern.

"Yeah I'm fine, just got caught up thinking about things," Emma said stuffing her equipment into her bag.

"You can't let that happen Emma, when you're here or when your doing work you need to be in the moment and you can't let distractions get in your head," Mulan offered her words of wisdom.

"Yeah I know, it won't happen again," Emma assured her before taking a long drink from her water bottle.

"Are you sure you're all right?" Mulan asked again.

"Yeah I'll see you Monday, have a good weekend," Emma said hoisting her bag over her shoulder and walking out of the gym to her car. She threw her bag into the back seat and got into her car and turned on the engine. She took and deep breath and took her hair out of its sweaty ponytail and ran her hands through her hair, lost in thought. Why was she almost haunted by the flash of hurt and confusion she saw in Killian's eyes when she didn't take his number? He wasn't the first guy she had shot down since the whole disaster that was her and Neal, so why was this one sticking in her mind? She tried to push thoughts of him and his too blue eyes and his thick dark hair to the back of her mind, telling herself that this would pass and that it was better for her to be alone, better for her to protect herself. She put her car into gear and pulled out of the gym parking lot and out onto the road, she turned on the radio to drown out the silence. She tapped along with the beat of the song and sang along softly not paying much attention to the lyrics and half wondered if she wanted to order a pizza or Chinese food for dinner since she really didn't feel like dinner.

"All right that was "Ships In the Night" by Mat Kearney and I certainly hope none of my listeners have that feeling, like they just met someone bloody brilliant only to be passed by, but I suppose that's how life works sometimes. Anyway up next we have "Riptide" by Vance Joy so I hope you all enjoy, and you are listening to "The Pirating Hour" with Killian Jones," a familiar accented voice said over the radio. Emma stared at her radio, trying to make sure she didn't just hallucinate what she just heard. Was he talking about her? Did he really think she was 'bloody brilliant' as he put it? Emma shook herself, the song could be about anyone just because she was on his boat last weekend and she didn't take his number didn't mean he would dedicate a song to her on the radio?

She pulled into her parking spot in her apartment complex's garage and walked up to her apartment. She took a long shower letting the warm water ease the stiffness in her shoulders and sooth her sore muscles but doing nothing to clear her mind of thoughts of Killian sitting alone at the radio station or the song that he played on the radio that was stubbornly stuck in her head. Emma hopped out of the shower and toweled off, catching herself humming the chorus to herself as she brushed her hair. She rolled her eyes at herself and walked into the kitchen and poured herself a healthy glass of wine before ordering a pizza and turning on her TV to watch Agent Carter. Emma and Clarke texted all through the hour, talking about how awesome Peggy was and Emma felt herself getting a bit teary when Peggy found out that Howard had Steve's blood in a vial. After the show Emma promised Clarke they'd hang out again that weekend and went to her desk with her pizza, her files, and her computer trying to track down a guy who had let his brother put his prized motorcycle up for bail before skipping town but she just couldn't concentrate. Emma tried to listen to some music to help her focus but nothing was working she ran a frustrated hand through her hair ad massaged her temples. She sighed because she knew exactly what song she needed to listen to and ended up downloading the damn song. She tried to tell herself that it was just because it was catchy but she knew deep down there was another reason, an attractive dark haired blue eyed reason.

Killian wrapped up his show and pushed his microphone away from him with a sigh before getting up from his chair. He felt like an ass for being so hung up on the woman from the past weekend, but he just never met a woman quite like Emma Swan, fierce and fiery with a dry sarcastic wit he was, for lack of better words, smitten with her. They had a natural flow with each other when they playfully teased and talked to each other while on his boat, so why did all that change when they got back to land? He shook his head and grabbed the CDs of new bands he needed to listen to before heading out of the studio.

"Hey Killian we're all going out for a drink, want to come?" Robin had asked as he, Will, and David shrugged on their jackets.

"Sure why not?" he said before following them out to their favorite bar and getting a pint.

"So what was up with that 'passing in the night' comment Jones?" David asked him, taking a sip of his beer.

"Yeah are you hung up on another girl?" Will joked.

"It's nothing just trying to connect to the audience as our dear station manager says," Killian said rolling his eyes. He could feel David's eyes lingering on him and took a long pull from his beer. "Let's go play a few rounds of pool, what do you say?" he suggested, hoping to pull the attention of his friends off of him. They played a few rounds of pool, Killian and David kicking Will and Robin's asses before Will caught sight of a very pretty blonde and went to go flirt with her.

Robin sighed and checked his watch, "Shit it's getting late I've got to get going, I'll see you all later," he said as he put on his jacket and walking out of the bar.

David and Killian walked back to the bar and ordered another round and sat in the barstools, David turned to Killian "Are you feeling all right?" he asked.

"Just fine, why do you ask mate?" Killian said.

"You just seem a little quieter and more brooding than usual," David noted with a shrug.

Killian sighed and put his glass down on the bar and turned to him, "Well I guess something may have been bothering me, but I'm not 'brooding' as you put it."

"Do you want to talk about it?" David asked him. Killian pondered for a moment as David patiently waited for his response.

"Fine, I can tell you won't let this go if I don't," David smirked at him a little but put his drink back on the bar and leaned toward Killian listening intently. "All right well Will was right and it is about a woman, I met her last weekend when Bellamy and I took her and her Little Sister out for a harbor cruise, I thought she and I were really hitting it off, she's funny and sarcastic and witty, and absolutely bloody brilliant but when we got to shore and I tried to give her my number she looked taken aback and refused to take it. And now I can't help but feel like a bit of a prat because obviously she didn't have to take my number, she's a grown woman and she doesn't owe me anything but I just thought it would have been nice to see her again," Killian confessed.

"Damn I'm sorry Killian that is not easy, it sucks to be rejected but like you said, she doesn't owe you her time but don't completely loose hope, she already has the email address for the harbor cruises maybe she'll suddenly realize that you're a good guy and drop you a line," David said and he placed a hand on Killian's shoulder. Killian smiled at him and gestured to the bartender to give them another round, they spent the rest of their night talking about the station and David's new girlfriend Mary Margaret before they called it a night. Killian caught a cab to his apartment, stumbling in and nearly knocking over the little table he keeps by his door. He stretched and took off his jacket, hanging it on its hook. He watered all his plants (well watered the areas _around _his plants for the most part) and fell face first onto his bed, not hearing the ping from his phone alerting him about a new message, already asleep.


	5. A Run in at Starbucks

Bellamy woke with a start at the sounds of his alarm and groaned before stumbling out of bed and into the kitchen to make some coffee. He poured a cup for himself and one for Octavia before quietly knocking on her door and going into her room to wake her up.

"O come on time get up," he said nudging her. Octavia groaned and rolled over pulling her sheets up to cover her face.

"Noooooooooo," Bellamy heard her whine and her chuckled, poking her again.

"Get up, I know you have a big test today."

"Fine but can we stop by Starbucks on the way?" Octavia asked pushing her bedsheets away from her face.

"If it'll help you to get your ass out of bed then fine. Just be quiet getting ready, Mom had to work the late shift again and she needs some sleep," Bellamy reminded her before heading out of her bedroom and into his room and sat at his desk and checked his email to see if any of his professors cancelled class (they didn't) and packed his bag for the day. He and Octavia quietly left the apartment and walked to the bus stop, Bellamy quizzing her from her large stack of history flashcards.

"All right who is Oppenheimer?" he asked, looking over the flashcard at his sister.

"He umm did something in World War II?" Octavia said massaging her temples.

"He was on the Manhattan Project and he helped develop the atomic bomb," Bellamy said somewhat smugly.

"Wipe that smug grin off your face Bell, I'm barely awake and not everyone is a huge history nerd like you," she said defensively. Bellamy laughed and put his arm around her shoulders.

"You'll do fine, don't worry, come on this is our stop," he said rising from his seat and grabbing his backpack. He and Octavia hopped off the bus and headed into the busy Starbucks around the corner from Octavia's school.

They got into line behind a blonde girl and Bellamy busied himself looking at the menu board, trying to decide what he wanted and tuned out his sister until he heard his name.

"What?" he said looking down at Octavia and instead meeting Clarke's eyes. He turned to Octavia a look of clear confusion on his face. "You two know each other?"

"Yeah, we were in the same art class last year, I thought I told you about her?" Octavia answered looking from Clarke to Bellamy, "How do you know each other?"

"We're in the same PoliSci class at Bunker Hill, I didn't realize you two were brother and sister," Clarke said, looking at Bellamy.

"Well now that we've all established how we know each other can you move the line forward?" a disgruntled man in a business suit behind them asked. Clarke rolled her eyes at him and turned to the barista and ordered her drink. Bellamy ordered his and Octavia's drinks and an extra one for Killian and moved over to the side to wait by the pick up area. Clarke raised her eyebrow at Bellamy when she saw the third coffee.

"What's with the extra coffee?" she asked.

"It's for Killian, I have some time to kill before my first class so I hang out at the radio station and help out," he explained grabbing both coffees and adding his preferred amount of cream and sugar.

"If you have that much time before class then why are you even up this early?"

"I knew O had a big test today and I wanted to help her out," he shrugged as if it was no big deal. Clarke looked at him with an expression he couldn't quite read and followed her out of the coffee shop where Octavia was already waiting for him, nonchalantly sipping her Frappachino.

"You want to walk together?" she asked Clarke. Clarke nodded and turned toward Bellamy.

"I'll see you in class then?" she said.

"Yeah I'll see you around Princess," he said with a smirk before turning to Octavia, "Good luck on your test, you'll do great," he smiled and handed her back her flashcards. Octavia smiled at him and turned with Clarke to walk in the direction of the high school. Bellamy watched them go a small smile still on his face before turning and walking a couple of blocks towards the radio station. Bellamy let himself into the station and headed to Killian's office, he knocked on the door only to find his Big Brother slumped over his desk with his head in his hands.

"You look like you had a rough night," Bellamy observed before placing the coffee in front of Killian. Killian groaned in response and took a long sip of his coffee before looking up at Bellamy.

"Bell I'm going to give you some Big Brother wisdom, when your my age don't go drinking on a weeknight, the morning will not be pleasant," he said running his hand through his hair. "Could you do me a favor? Go over the emails for the harbor cruises and put the reservations on the calendar? I need to find some Advil before I even look at my damned computer." Killian muttered rising from his desk chair and walking out of the office. Bellamy chuckled and sat down in front of the computer and checking the email for Jolly Roger Harbor Cruises, putting all the requested dates onto Killian's Google Calendar, finding the usual anniversary, office team building, family bonding and tourist requests until he found an email from an eswan815 with the subject line "Song Request." Bellamy slightly confused opened it and saw:

"_So I was listening to your show tonight in the car and I wanted to request a song, or is that how you put it "bad form"? Maybe we could talk more about it in person? Let me know. -Emma Swan"_

Bellamy smiled, he had officially won his bet with Clarke he thought to himself smugly, the thought of an almost guaranteed A on his final paper now that he had Clarke's help.

"What's that big grin for Bell?" Killian said striding back into the office.

"Oh nothing, but it looks like you got an interesting email," he pointed to the screen, Killian came around his desk and read the email over Bellamy's shoulder. Bellamy saw his Big Brother's face light up and one of the biggest and goofiest grins spread across his face. He realized he hadn't seen Killian this happy about getting an email from a woman in a long long time.

"So what are you going to say?" he asked getting up from the desk chair.

"That we could meet and talk about her music requests over drinks," Killian said already hitting the reply button with vigor.

"You sure that's the best idea? I mean she seems pretty skittish, maybe it's best to try over coffee or something casual?" Bellamy suggested. Killian stopped his typing and looked at Bellamy with a ponderous expression.

"Perhaps you're right lad, thanks for the advice," he said and turned back to his computer. Bellamy checked the time and saw that he had class soon.

"I gotta go, promise me you won't go overboard?" he said hitching his backpack around his shoulders and hurrying out the door. He only just made it onto his bus that'll take him to his school just in time for his Classical Mythology lecture, praying to every deity he knew that Killian would not screw up his chances.

Clarke got onto the bus to Bunker Hill with Monty in tow, glad that she had a friend who was also dual enrolled in a class at the community college. She listened to him talk about his day and about his engineering class that he was taking, while she thought about something Octavia had said to her when they walked to school together.

"Do you like my brother?" Octavia had asked her point blank once Bellamy was out of earshot.

"What? No!" Clarke had asked trying to ignore the heat that was radiating for her cheeks.

"I mean it's okay if you do, I'm just asking but you too were totally making eyes at each other," Octavia commented and took a slow sip of her frap.

"We were not making eyes, we were just observing the fact that we both know you and have an unexpected connection," Clarke answered, choosing her words very carefully.

"Uh huh, all right I'll take your word for it," Octavia nodded a smirk plastered on her face, a smirk that was nearly identical to Bellamy's.

"Ummm Clarke?" Monty's voice called her back to earth.

"What? sorry I kind of zoned out, long day," she explained. Monty gave a noncommittal shrug.

"It's okay, it happens. But this is our stop," he gathered up his things and stood letting her walk into the aisle and off the bus before him. She waved goodbye to Monty before heading to the building her Poli Sci class was in and sitting in her usual seat towards the front. She had her laptop open and on and began going over her notes from the last class when she saw a tall and dark figure flop into the desk next to her.

"Looks like I've already won the bet Princess," he said smirking that stupid smirk at her.

"What do you mean and don't you usually sit in the back with your friend?" she questioned looking back towards that kind of creepy kid Bellamy sat next to.

"Murphey can take care of himself for one class, and you Big Sister asked my Big Brother out last night so now you have to help me with my final paper," he proclaimed smugly.

"So wait, Emma Swan actually said "let's go on a date" to Killian?" Clarke asked.

"Well no, not in so many words but she asked to talk about music with him in person and not just over email," Bellamy explained his face looking distinctly less smug.

"That doesn't mean it's a date, that could mean she just wants to talk about music and be friends with Killian considering he's a radio dj," Clarke said "Just because a man and a woman hang out does not mean it's a date." she explained, feeling a grateful for being on debate team last year.

"Oh come on, it's a date and you know it," Bellamy snapped at her, crossing his arms in front of him.

"No it's not, God that is such a male entitled view, just because a woman wants to discuss music with someone who works in music she's automatically interested? Newsflash people men and women can hang out together with out it being a date, would you consider when we went to the library to dig up dirt on our Big Siblings a date?" she snapped.

Bellamy stared at her, mouth slightly agape and Clarke could see the wheels turning in his head trying to figure out a counter argument.

"Fine, it's not a date then, but hey who says friendships can't turn into something more?" he winked at her and turned to the front where Kane was starting his lecture. Clarke tried to focus and take notes but couldn't help thinking of that smirk that he and Octavia shared and had to stop herself from sneaking glances at him, only to find him sneaking glances at her.


End file.
